Formic Acid → HCID 13206170, compound

Participants

Reaction Steps

A solution of 0.1 g of 2-aminomethyl-3-(4-methoxycarbonylbutyl)pyridine in 0.6 ml of formic acid is heated at 90° for 18 hours. The mixture is cooled to 0°, made basic with saturated ammonium hydroxide solution and extracted with methylene chloride (4×10 ml). Drying, filtration and evaporation of the extracts yields 2-(N-formylaminomethyl)-3-(4-methoxycarbonylbutyl)pyridine, melting at 43°-45° C. which is redissolved in 1 ml of toluene and heated at 90° for 17 hours with 75 mg of phosphorus oxychloride. Evaporation of excess phosphorus oxychloride with toluene, basification at 0° with saturated ammonium hydroxide solution, extraction with methylene chloride (4×15 ml) and drying over sodium sulfate yields an oil, which is chromatographed (silica gel, ethyl acetate) to yield as an oil, 8-(4-methoxycarbonylbutyl)-imidazo[1,5-a]pyridine; Rf 0.29; NMR (CDCl3) 3.70 (s, 3 H), 6.50 (d, 2 H), 7.43 (s, 1 H), 7.83 (t, 1 H), 8.22 (s, 1 H); IR (CH2Cl2) 1725 cm-1.

Provenance & Evidence